Coastal Sailing in Maine

A Week of Coastal Sailing in Maine Onboard the Windjammer Angelique

There are over 4,600 islands off the long, rugged coast of Maine, and no better way to explore them than sailing through the bays and narrows on a tall wooden ship (aka, windjammer). The pristine beauty of nature, wildlife sightings, and expansive sunrises over the water offer a unique perspective truly unlike any other kind of tourism.

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When I was presented with the opportunity to join a group of women for the sailing adventure of a lifetime in Coastal Maine, it didn’t take but a couple hours to clear my calendar, line up flights, and say “yes.”

Maine has been on my “list” for a while, but sailing not so much. My husband isn’t a fan. So, I knew if I ever wanted to do it, this was my chance. And looking back, I can honestly say it was an unforgettable and awe-inspiring experience.

Above photo: Aerial view of islands off the coast of Maine (left); Old school navigation (right)

What is a windjammer cruise?

The premise of windjamming is sailing “destination unknown.” Although most of these tall wooden boats are equipped with navigation technology and motors, they sail old-school, eco-friendly style as long as there is wind. For that reason, there is no upfront itinerary except that you will be on the boat for whatever duration you’ve signed up for. This makes it one of the easiest trips you will ever plan.

Our trip was a private charter of 25 women all connected to each other through mutual friends and family. But, whether a private charter or themed cruise, an authentic Maine experience awaits.

This post will break down our day by day journey, but mostly focus on the experience of being onboard the boat for a week. Every sail is different. Hence, the question isn’t about following a specific itinerary, but what to expect as the winds chart your course.

Above photos: Sailing in Penobscot Bay

Our June trip took us through Penobscot and Jericho Bays. Each evening, the Angelique moored in a different harbor. Come morning, we let down the dinghy and rowed over to shore to enjoy nature, hiking, and occasionally a little shopping before pulling up anchor and sailing to our next mystery destination.

Above photos: Windjammer Sailing

While each stop on our journey was a new invitation to explore (and stretch our sea legs!), getting there was at least half the fun. For one, there is the opportunity to join the crew in chores, hoisting the sails, and navigating. But, if that’s not your thing, soaking up the sun, ocean breeze, and spectacular scenery is what life onboard is all about.

Above photos: Life onboard the Windjammer Angelique (left and center); Captain Dennis (right)

Above photos: Lighthouses, seals, and lobster boats

Our stops included:

• Camden Historic Downtown
• Swan’s Island
• Big Babson Island
• Castine
• Holbrook Island Sanctuary
• Camden Harbor

Camden Historic Downtown

The Windjammer Angelique harbors in Camden Harbor, a small but well-protected cove in Penobscot Bay. Before boarding, we had some time to explore the area. This quintessential New England town is known for its historic architecture, waterfront parks, and harbor full of sailboats. Of course, we returned to Camden Harbor at the end of our sailing.

Above photos: Camden

Swan’s Island

Our first stop was Swan’s Island, a town with a population around 350. The short walk up to Burnt Coat Harbor Lighthouse afforded us a glimpse of a completely different way of life. More on this classic coastal village here.

Above photo: View of Swan’s Island from Burnt Coat Harbor

Above photos: Swan’s Island

A complete post of our visit to Swan’s Island can be found here.

Big Babson Island

From Swan’s Island, the prevailing winds took us to the Babson Island Preserve. This gorgeous, protected conservation area has a trail going through fern meadows and a pinecone littered forrest. Bug repellant and binoculars are a must!

Above photo: The shoreline of Big Babson Island

The beach area at Babson Island Preserve is also where we set-up camp for a perfect summer Maine lobster bake. This all-you-can-eat feast was a highlight of the week — and truly something you can only authentically experience in Maine. More photos and details here.

Above photos: Maine lobster bake

A complete post of our Lobster Bake at Babson Island Preserve can be found here.

The sun rises early in June in Maine (4:52 am). And, if you are a light sleeper, it is hard to resist not going up on deck to watch the harbor porpoises and seals playing the in water once the light breaks through your cabin skylight. You never know what little critters will show up to greet you in the still of the morning. Imagine this: no one else is up except the kitchen crew, you have a warm cup of coffee in your hands, seals splashing around the distant rocks, and the sun peaking over the tree line. It is truly as incredible as it sounds.

Above photos: The most spectacular sunrises and sunsets

Castine

One of the aspects of travel that I thoroughly enjoy is learning about the history of an area. I got a hearty dose of this at our next stop in Castine, Maine. The Revolutionary War and Maritime history here is deep. If there was one place I wish I had been able to spend more time, it was here in Castine. More about Castine here.

Above photos: Abbott School, Castine Historical Society (left); United Unitarian Congregation (right)

A complete post of our visit to Castine can be found here.

Holbrook Island Sanctuary

Following our afternoon in Castine, we moored overnight just a stone’s throw away offshore at Holbrook Island Sanctuary. The following morning, we loaded up the dingy with oars-in-hand, rowed over to the reserve trailhead, and had a beautiful walk.

Above photo: Early morning off of Holbrook Island Sanctuary

Above photos: Holbrook Island Sanctuary

Camden Harbor

Our final day of sailing took us back to Camden Harbor with a marina full of colorful vessels and watchful tourists.

Above photos: Curtis Island Lighthouse (left); Harbor Seal (center); Camden Harbor (top and right)

Windjammer Angelique

More information about Captain Dennis and The Windjammer Angelique, including future sailing dates and reservation details, is available here: Windjammer Angelique

Above photo: The Windjammer Angelique

There are only a handful (less than 20) owner-operated schooners that operate multi-night trips in Maine. There are dozens of others that offer day sailings. Not all of these harbor in Camden. I’ve noted others that sail from Portland and Rockport. We spotted a few of these other vessels while we were out sailing.

Above photos: Wooden boats at sea

For more information about the Windjammer fleet in Maine and to peruse the schedule of sailings, visit the Maine Windjammer Association website here.

If you are looking for something shorter in duration or a private charter, there are other schooners that sail from Portland and Boothbay Habor. Here are a few options:

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